Your Full Guide to Every ‘Supernatural’ Romance: Who Are Sam, Dean & Castiel’s Love Interests?
“Romantic” isn’t the first word we’d use to describe Supernatural, which is all about the brotherly love between Sam (Jared Padalecki) and Dean (Jensen Ackles). It makes sense, given that relationships don’t really gel with the Winchesters’ line of work. Monster-hunting puts them on the road and in constant danger, and it’s not uncommon for people that they cross paths with to become casualties.
Still, Supernatural couldn’t have gone 15 seasons without introducing at least a few love interests for its main trio, which includes the brothers’ angel companion, Castiel (Misha Collins). Though quite a few of their entanglements are brief and/or don’t pan out, Dean, Sam, and Castiel have a few romances that leave a lasting impression. Swooon has broken down all of the characters’ most important romantic relationships from the start to the end of the show.
Who are Sam’s love interests in Supernatural?
Sam has the most love interests out of all the characters in the show. The death of his fiancée, Jessica Moore (Adrianne Palicki), in Season 1 is what gets him back into the monster-hunting game, remember? From there, Season 1 gives Sam an episode-long thing with Lori Sorensen (Jane McGregor) and a quick romance with Sarah Blake (Taylor Cole), though he ends both because he’s still not over Jess. (Sara returns in Season 8 only to be killed by Mark Sheppard‘s Crowley.)
Season 2 gives him werewolf Madison (Emmanuelle Vaugier), while the next two are dedicated to Sam’s toxic relationship with demon Ruby (first played by Katie Cassidy, then Genevieve Padalecki, who later became Padalecki’s wife). Under a love spell, Sam almost gets married to superfan Becky (Emily Perkins) in Season 5, but he gets out of it. Season 7 puts Amy Pond (Jewel Staite) back in Sam’s life, after she gave him his first kiss when they were teenagers. She turns out to be a monster, and when Dean kills her in Season 7, Sam struggles to forgive him.
Season 8’s love interest is veterinarian Amelia (Liane Balaban) and it takes three more seasons for Sam to find another serious connection with Eileen (Shoshannah Stern), a deaf monster-hunter. The romance tapers off after she “dies,” though Sam shares a kiss with Velma (Kate Micucci) in its one-off Scooby Doo-themed episode.
Keep scrolling for the full rundown of Sam’s most significant relationships — including who he ends up with.
What happens between Sam & Jessica?
The show begins with Sam studying law at Stanford University, with his serious girlfriend Jessica by his side. Sam’s forced to start hunting again when Jessica, with whom he was living with at the time, is killed by a demon. She’s suspended on the ceiling and set on fire, dying the same way that Sam and Dean’s mom did.
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What happens between Sam & Madison?
Madison’s appearance is brief, but she’s the first person whom Sam really allows himself to fall for after Jessica. In fact, Madison is later pointed out as “the first woman since Jessica he really loved,” which makes Season 2’s Episode 17, titled “Heart,” even more heartbreaking. When the brothers go on a werewolf hunt, they meet Madison. They think her ex is involved with the killings, so Sam guards her and bonds with her in the process. Ultimately, though, Madison is revealed to be the werewolf, though she doesn’t retain her memories when she transforms. She asks Sam to kill her, and he does.
What happens between Sam & Ruby?
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Sam and Ruby have one of the longer and more complicated relationships on Supernatural, but we’ll attempt to give you the gist. Ruby first enters the picture when she, Sam, and Dean reluctantly join forces to stop the demon Lilith in Season 3. (Reluctantly, since Ruby is a demon herself.) When Sam discovers that he has demon blood in him, she encourages him to lean into his darker side and hone his powers. She gets him addicted to demon blood to enhance them, and their romantic bond deepens.
Ultimately, we find out that Ruby has had an ulterior motive all along: Sam has the ability to free Lucifer (Mark Pellegrino), so Sam is the only one who ever had real feelings in their relationship. All is revealed in the Season 4 finale, which sees Dean deliver the final blow to Ruby with Sam’s help.
What happens between Sam & Amelia?
After Dean disappears into Purgatory, the start of Season 8 finds Sam in a relationship with Amelia. They meet when he accidentally hits a dog, so he takes it to the vet, where Amelia works. They connect because they have both experienced loss. Amelia’s husband died at war… but he actually didn’t. She finds out that he’s actually still alive, so Sam breaks up with her so they can reunite.
Sam and Amelia cross paths again after Dean’s return, and feelings are still there. Amelia suggests they meet up at a motel later if they want to be together. She shows up, but Sam ultimately chooses hunting and his brother over her in Episode 10.
What happens between Sam & Eileen?
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Sam and Eileen meet in Season 11, hunting the banshee that killed Eileen’s parents and made her lose her hearing. Since they’re both familiar with the hunting life, they become friends, but their relationship doesn’t really get a chance to get off the ground. Eileen is killed by Arthur Ketch’s (David Haydn-Jones) hellhound, leaving Sam devastated.
Eileen returns as a ghost in Season 15, and Sam manages to resurrect her. That’s when their relationship really takes off, living together with Dean in the Men of Letters bunker. It turns out, though, that Rob Benedict’s God was the one pulling the strings, and he even sparked Sam and Eileen’s romance. They take a break when Eileen is uncertain if the feelings they have are real.
Soon, God starts wiping everyone out, including Eileen. Sam tries to save her but doesn’t make it in time. Luckily, Jack (Alexander Calvert) brings everyone back to life by the show’s end, Eileen included.
Who does Sam end up with in Supernatural?
After the events of Supernatural’s Season 15 series finale, Sam lives out his life with an unnamed wife and family. Her face is never shown, but showrunner Andrew Dabb told TV Guide Magazine, “We wanted someone there, so it wasn’t like there was no female presence at all. But at the same time, do you cast someone totally brand new that the audience will have not seen before? Or do you keep it a little vague and people can imply whatever they want to imply?”
The episode was shot during the COVID-19 pandemic, so they couldn’t bring in Stern for filming, even though they were “building toward” Eileen marrying Sam. “I’m not saying they wouldn’t have done [made Eileen Sam’s wife],” Dabb continued. “They may have. The logistical challenge of bringing a lot of people in, being the first show up during COVID, was just not feasible on our end.”
Who are Dean’s love interests in Supernatural?
Like Sam, Dean is pretty unlucky in love, though he’s never lacking in hookups. In Season 1, we do find out he’s been in a long-term relationship at one point, with non-hunter Cassie Robinson (Megalyn Echikunwoke). Next season, Dean has a brief thing with Carmen Porter (Michelle Borth), but she’s not real. (A djinn puts Dean in a trance and creates Carmen as his ideal girlfriend.) Dean also flirts with his friend and fellow hunter Jo Harvelle (Alona Tal) over the next few seasons before her death.
His strongest relationship is with Season 3’s single mom Lisa Braeden (Cindy Sampson) before lifestyle differences tear them apart. An angel, Anna (Julie McNiven), catches his eye in Seasons 4 and 5. Amara (Emily Swallow), aka the Darkness and God’s twin sister, takes an interest in Dean in Season 11, and that’s pretty much that in the way of romances. (Unless we count Castiel, but more on that below.)
Find the breakdown of Dean’s most significant relationships — including who he ends up with — below.
What happens between Dean & Cassie?
Dean and Cassie meet before the events of the show, when Dean is on a hunting trip with his dad. Once their relationship deepens, Dean tells her about monsters and hunting. She can’t cope with it, so their relationship ends. They reunite in Season 1 Episode 13, “Route 666,” when Cassie needs Dean’s hunting skills. They hook up, but ultimately part for the same reason they did in the past.
What happens between Dean & Jo?
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Technically, nothing romantic happens between Dean and Jo. A hunter like the Winchesters, Jo and Dean’s energies match when we see them interact for the first time in Season 2. But while Jo has a crush on Dean and makes no attempts to hide it, Dean views her more as family. Shortly after they meet again in Season 5, they kiss for the first time. It’s a goodbye kiss: Jo sacrifices herself to save the Winchester brothers in Episode 10, “Abandon All Hope…”
What happens between Dean & Lisa?
Dean and Lisa hooked up in the past before we see them interact for the first time in Season 3. When he’s on a hunt in her area, Dean unexpectedly hits her up, even though it’s been years since they last spoke. Dean meets her son, Ben, and she quickly clarifies that he’s not Dean’s son. Dean has a dream about having a life with Lisa, but they part ways once the hunt is over.
In Season 5, Dean visits Lisa again, knowing the apocalypse is coming. Once Sam sacrifices himself to Lucifer at the end of the season, Dean seeks solace in Lisa once again, and he tries to have a normal life with Lisa and her son afterward, retiring from hunting. When he discovers Sam is alive about a year later, Dean gets sucked back into the monster-hunting world. He and Lisa try to make it work, but it goes downhill from there. In Season 6’s penultimate episode, Lisa and Ben are kidnapped by Crowley, so Dean asks Castiel to erase their memories of him once they’re safe.
What happens between Dean & Anna?
Dean is drawn to Anna in Season 4, and they find comfort in each other, despite Dean figuring out that she’s an angel. Dean recently escaped Hell, and Anna sympathizes with him and understands his pain. It leads to a hook-up in Episode 10, but it fizzles out. She ultimately betrays Dean when, a season later, she tries to stop the apocalypse by going back in time and killing Mary and John Winchester, which would have stopped Sam’s birth. (She doesn’t succeed, obviously, and dies.)
What happens between Dean & Amara?
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Dean and Amara/The Darkness are a tricky case, since it’s not really romantic, and she’s one of the oldest entities in the universe and capable of ending the world. It’s difficult to sum up this complicated relationship, but it starts when Dean releases The Darkness by removing the Mark of Cain from his arm in Season 11. A bond manifests between them from then on, making it so he can’t kill her, and she has a soft spot for him.
In Episode 9, Amara consumes some innocent people, which Dean isn’t happy about, but one thing leads to another, and Amara kisses Dean. He returns it briefly. From then on, Dean doubts his ability to resist Amara, and they engage in some more will-they-won’t-they behavior until Dean almost follows through with killing her, and Amara leaves Earth behind. She shows up again in Season 15, but the strange romantic undertones are gone.
Who does Dean end up with in Supernatural?
No one. Dean dies on a hunt in the Season 15 finale, so he doesn’t get to find a happily ever after with a special someone. Dean’s just cruising around Heaven in the Impala before he reunites with Sam decades later in the afterlife. (The ending drives the point home again that brotherly love is the heart of the story.)
Who are Castiel’s love interests in Supernatural?
Castiel doesn’t pursue nearly as many romantic relationships as Sam and Dean do, which makes sense given that he’s an angel inhabiting a human body on Earth. How is he supposed to connect with normal people? Still, he does manage to get some action. First, there’s demon Meg (Rachel Miner) in Seasons 6 and 7. He hooks up with reaper April Kelly (Shannon Lucio) in Season 9, though it never becomes something more. Amnesiac Cas marries Daphne Allen (Johanna Marlowe) in Season 7, but leaves her once he regains his memories. Finally, Cas delivers that famous love confession to Dean in Season 15.
What happens between Castiel & Meg?
As an angel on the side of Heaven and a demon sworn to Lucifer, Cas and Meg start off as enemies in Season 5. They become reluctant allies in the next season, and Meg’s flirty, suggestive comments get responses out of Cas, whom she nicknames Clarence. They kiss in Season 6’s tenth episode, at first out of necessity, but then Cas kisses her again with more passion behind it. (That’s when he delivers his famous “pizza man” line.)
The romantic undertones last through Season 7 and 8, though they never develop into anything serious. Well, we suppose it is serious for Cas, since he doesn’t really express interest in anyone else until Season 15. Meg’s feelings came across stronger than his, and she sacrifices herself to buy Cas and the Winchesters time in Season 8 Episode 17, “Goodbye Stranger.”
What happens between Castiel & Dean?
Now, this one’s a loaded question. Too much happens between Cas and Dean for us to chronicle it all here, starting from when Cas rescues Dean from Hell at the start of Season 4. From there, they become allies and eventual friends, developing a deep and unbreakable bond. It was never confirmed to be romantic on Dean’s part. But in Season 15 Episode 18, “Despair,” Cas saves Dean from Death by sacrificing himself, and his feelings for Dean are revealed before he dies.
Cas had made a deal with the Empty — it could claim him after he experiences true happiness. He achieves that feeling when he says “I love you” to Dean, disappearing into The Void and taking Death with him. (Surely, that’s not a platonic declaration of love, right? We suppose it’s up to interpretation, though Collins has his take.)
Who does Castiel end up with in Supernatural?
Like Dean, Cas ends up with no one, since he bites the dust. Destiel shippers don’t get their happy ending, we’re afraid, though maybe one love confession is better than nothing.
Let us know your favorite Supernatural romance in the comments below!
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